Dehydrogenation and dehalogenation of amines in MALDI-TOF MS investigated by isotopic labeling

doi:10.1002/jms.3296

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	Dehydrogenation and dehalogenation of amines in MALDI-TOF MS investigated by isotopic labeling
	Kang, Chuanqing 1; Zhou, Yihan 2; Du, Zhijun 1; Bian, Zheng 1; Wang, Jianwei 2; Qiu, Xuepeng 1; Gao, Lianxun 1; Sun, Yuequan 2
刊名	JOURNAL OF MASS SPECTROMETRY
	2013-12-01
卷号	48 期号:12 页码:1318-1324
关键词	Dehydrogenation Amines Isotopic Labeling Mass Spectroscopy Dehalogenation
ISSN号	1076-5174
DOI	10.1002/jms.3296
英文摘要	Secondary and tertiary amines have been reported to form [M-H](+) that correspond to dehydrogenation in matrix-assisted laser desorption ionization time of flight mass spectrometry (MALDI-TOF MS). In this investigation, we studied the dehydrogenation of amines in MALDI-TOF MS by isotopic labeling. Aliphatic amines were labeled with deuterium on the methylene of an N-benzyl group, which resulted in the formation of [M-D](+) and [M-H](+) ions by dedeuteration and dehydrogenation, respectively. This method revealed the proton that was removed. The spectra of most tertiary amines with an N-benzyl group showed high-intensity [M-D](+) and [M-H](+) ion peaks, whereas those of secondary amines showed low-intensity ion peaks. Ratios between the peak intensities of [M-D](+) and [M-H](+) greater than 1 suggested chemoselective dehydrogenation at the N-benzyl groups. The presence of an electron donor group on the N-benzyl groups enhanced the selectivity. The dehalogenation of amines with an N-(4-halobenzyl) group was also observed alongside dehydrogenation. The amino ions from dehalogenation can undergo second dehydrogenation. These results provide the first direct evidence about the position at which dehydrogenation of an amine occurs and the first example of dehalogenation of haloaromatic compounds in MALDI-TOF MS. These results should be helpful in the structural identification and elucidation of synthetic and natural molecules. Copyright (c) 2013 John Wiley & Sons, Ltd.
语种	英语
出版者	WILEY-BLACKWELL
WOS记录号	WOS:000328252800010
内容类型	期刊论文
源URL	[http://ir.iccas.ac.cn/handle/121111/46511]
专题	中国科学院化学研究所
通讯作者	Kang, Chuanqing
作者单位	1.Chinese Acad Sci, Changchun Inst Appl Chem, State Key Lab Polymer Phys & Chem, Changchun 130022, Peoples R China 2.Chinese Acad Sci, Changchun Inst Appl Chem, Natl Analyt Res Ctr Electrochem & Spect, Changchun 130022, Peoples R China
推荐引用方式 GB/T 7714	Kang, Chuanqing,Zhou, Yihan,Du, Zhijun,et al. Dehydrogenation and dehalogenation of amines in MALDI-TOF MS investigated by isotopic labeling[J]. JOURNAL OF MASS SPECTROMETRY,2013,48(12):1318-1324.
APA	Kang, Chuanqing.,Zhou, Yihan.,Du, Zhijun.,Bian, Zheng.,Wang, Jianwei.,...&Sun, Yuequan.(2013).Dehydrogenation and dehalogenation of amines in MALDI-TOF MS investigated by isotopic labeling.JOURNAL OF MASS SPECTROMETRY,48(12),1318-1324.
MLA	Kang, Chuanqing,et al."Dehydrogenation and dehalogenation of amines in MALDI-TOF MS investigated by isotopic labeling".JOURNAL OF MASS SPECTROMETRY 48.12(2013):1318-1324.